6-Chloro-5-nitropyridine-3-carboxylic acid → 5-Amino-6-chloropyridine-3-carboxylic acid
Reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[NH2:11][C:10]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 6-chloro-5-nitronicotinic acid in acetic acid (240 ml) was added iron (20 g) and the mixture was heated with stirring on a steam bath. After 11/2 hours, the mixture was filtered hot and washed with hot acetic acid. The filtrate was concentrated to dryness and the residue was treated with 10% NaOH, filtered and the pH adjusted to 2-3. The solid was filtered to yield 8.0 g (60% yield) of 5-amino-6-chloronicotinic acid.
Workup
- temperaturethe mixture was heated
- filtrationAfter 11/2 hours, the mixture was filtered hot
- washwashed with hot acetic acid
- concentrationThe filtrate was concentrated to dryness
- additionthe residue was treated with 10% NaOH
- filtrationfiltered
- filtrationThe solid was filtered
Sources & evidence
- ORD record
- ord-a3289f514de64e9aaad3b598e675d697
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04279913
Reaction notes
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